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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H33F3N2O5S
Molecular Weight 602.664
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIPRANAVIR

SMILES

CCC[C@@]2(CCC1=CC=CC=C1)CC(O)=C([C@H](CC)C3=CC=CC(NS(=O)(=O)C4=NC=C(C=C4)C(F)(F)F)=C3)C(=O)O2

InChI

InChIKey=SUJUHGSWHZTSEU-FYBSXPHGSA-N
InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

HIDE SMILES / InChI

Description

Tipranavir (PNU-140690, trade mark APTIVUS) is a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. Tipranavir has potent in vitro activity against a variety of HIV-1 laboratory strains and clinical isolates, including those resistant to ritonavir, as well as HIV-2. The drug is launched in several countries, including the US and in the EU. APTIVUS, co-administered with ritonavir, is indicated for combination antiretroviral treatment of HIV-1 infected patients who are treatment-experienced and infected with HIV-1 strains resistant to more than one protease inhibitor.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
APTIVUS
PubMed

PubMed

TitleDatePubMed
Structure-based design of HIV protease inhibitors: sulfonamide-containing 5,6-dihydro-4-hydroxy-2-pyrones as non-peptidic inhibitors.
1996 Oct 25
Antiviral activity of the dihydropyrone PNU-140690, a new nonpeptidic human immunodeficiency virus protease inhibitor.
1997 May
In vitro combination of PNU-140690, a human immunodeficiency virus type 1 protease inhibitor, with ritonavir against ritonavir-sensitive and -resistant clinical isolates.
1997 Nov
Tipranavir (PNU-140690): a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class.
1998 Aug 27
In vitro antiviral interaction of lopinavir with other protease inhibitors.
2002 Jul
Activity of human immunodeficiency virus type 1 protease inhibitors against the initial autocleavage in Gag-Pol polyprotein processing.
2012 Jul
Novel method to assess antiretroviral target trough concentrations using in vitro susceptibility data.
2012 Nov
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
GRL-0519, a novel oxatricyclic ligand-containing nonpeptidic HIV-1 protease inhibitor (PI), potently suppresses replication of a wide spectrum of multi-PI-resistant HIV-1 variants in vitro.
2013 May
P2' benzene carboxylic acid moiety is associated with decrease in cellular uptake: evaluation of novel nonpeptidic HIV-1 protease inhibitors containing P2 bis-tetrahydrofuran moiety.
2013 Oct
Substrate envelope-designed potent HIV-1 protease inhibitors to avoid drug resistance.
2013 Sep 19
Patents

Sample Use Guides

In Vivo Use Guide
Adults: 500 mg APTIVUS® (tipranavir), co-administered with 200 mg ritonavir, twice daily. Pediatric patients (age 2 to 18 years): Dosing is based on body weight or body surface area not to exceed adult dose.
Route of Administration: Oral
In Vitro Use Guide
Tipranavir inhibits the replication of laboratory strains of HIV-1 and clinical isolates in acute models of T-cell infection, with EC50 ranging from 0.03 to 0.07 µM (18-42 ng/mL)
Name Type Language
TIPRANAVIR
EMA EPAR   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
TIPRANAVIR [WHO-DD]
Common Name English
3'-((1R)-1-((6R)-5,6-DIHYDRO-4-HYDROXY-2-OXO-6-PHENETHYL-6-PROPYL-2H-PYRAN-3-YL)PROPYL)-5-(TRIFLUOROMETHYL)-2-PYRIDINESULFONANILIDE
Systematic Name English
TIPRANAVIR [MART.]
Common Name English
TIPRANAVIR [EMA EPAR]
Common Name English
TIPRANAVIR [ORANGE BOOK]
Common Name English
APTIVUS
Brand Name English
TIPRANAVIR [INN]
Common Name English
TIPRANAVIR [VANDF]
Common Name English
TIPRANAVIR [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000246
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
NCI_THESAURUS C97366
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
EMA ASSESSMENT REPORTS APTIVUS (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
WHO-VATC QJ05AE09
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
LIVERTOX 969
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
WHO-ATC J05AE09
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
NDF-RT N0000175889
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
Code System Code Type Description
RXCUI
190548
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY RxNorm
CAS
174484-41-4
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
WIKIPEDIA
TIPRANAVIR
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
PUBCHEM
54682461
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
MESH
C107201
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
HSDB
174484-41-4
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
MERCK INDEX
M10885
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL222559
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
EVMPD
SUB04883MIG
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
EPA CompTox
174484-41-4
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
NCI_THESAURUS
C66603
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
DRUG BANK
DB00932
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
LactMed
174484-41-4
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY
INN
7774
Created by admin on Mon Oct 21 19:46:26 UTC 2019 , Edited by admin on Mon Oct 21 19:46:26 UTC 2019
PRIMARY